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It's the fourth annual "… of the year" extravaganza, in which Jesse Wilson and I each bestow 20 highly coveted and equally made up awards based on 2016's technology news.

Some of the awards include classics like “moonwalk of the year” and “lipstick on a pig of the year”, as well as new entries like “you dropped the ball at the finish line of the year” and special one I felt obliged to add for myself titled “biggest personal egg on face moment of the year”.

Supreme iOS/Mac engineer and Apple aficionado Ben Sandofsky joins me to break down Apple's September 2015 event. We dig into all the details of the iPhone, iPad and Apple TV announcements, with detailed discussion on why the iPad Pro was even necessary, the Internet's reaction to the Apple Pencil, the types of games we may and may not see on Apple TV, our fears for 3D Touch and more.

We also give our initial impressions of what was the most unexpected and perhaps bigggest announcement, that of the iPhone Upgrade Program, as well as discussing iCloud's stingy data caps, the 16GB base model iPhone and whether Apple's vastly increased product count and increasinly long keynotes are a worrying sign for the company.

To close out the show, Ben gives some insight into his time as a technical advisor for HBO's Silicon Valley series.

Guest Ron Amadeo and I discuss all the Alphabet related news of the week. We dig into why we think Google have made this move, discuss Sundar Pichai's continued rise, speculate idly on what companies Google might consider acquiring given their new structure and more.

Ron also provides some insight and impressions on the newly announced Galaxy Note 5, and we close things out discussing Stagefright and HTC's financial woes.

In the second and final part of my chat with Pushbullet CEO Ryan Oldenburg, we discuss how Pushbullet handles multi-platform development, how slower app review processes impact momentum and how the company deals with educating users who don't understand why some features don't work on other platforms.

Ryan also talks how much concern he has for Google potentially entering the space, as well as discussing the potential risk of adding confusion to Pushbullet with a focus on messaging, the app's usage of encryption and more.

In the first of a two part conversation, Ryan details the origin of Pushbullet and his usage of Android, why he decided to start a company and we compare notes on how a typical launch day goes for each of us. Ryan also details how he spends his time now that he is CEO of a company with seven employees, and we discuss that old chestnut of dealing with user feedback and providing support.